Having a hard time with a man at work

Can you keep a log of all the comments because if its a small company then your HR function - I suspect might be just your manager who fields all things.

Write in detail so you can present it to your manager as an accomplished fate i.e. "You need to do something about Bob because on 13th February he said xyz at 4pm then on the following Tuesday he said abc..."

Take no prisoners in this regard.

If he is so empathetic towards women then I think you should share the trials and tribulations of being a woman with him.

"Bloody hell Jeffrey, my periods come early, can you run to the shop and buy me some tampons . Supersize please. And while you're out can you nip into m and s and get me some clean knickers."

Is this all happening in working time or break time?

You could complain to your manager about your working time being taken up by him (depends on organisational culture re chit chat while working).

You should complain about being targeted for sexist harrassment because you're a woman.

I think my response would depend on whether I thought he was winding me up, or honest but idiotic. Both seem possible, but if it's the latter, I'd expect that maybe he was more generally akward and socially clueless. Some people are like that and come up wih crazy theories and generalisations to explain behaviours they don't understand.

If it's the first, I'd probably just ignore it, though I'd be tempted to be a smart ass. But it's probably not worthwhile at work. If the second, I'd be a little kinder, and maybe ask a well-placed question here and there. But mostly it's good to cultivate an attitude where people's stupid comments just pass over you.

You shouldn't have to devise strategies for dealing with this. If some arsehole at work was mouthing off about 'gays' or 'Jews' there'd be uproar. This is no different and your manager needs to get a grip, pronto.

Your problem is your weak, ineffectual manager.

Small companies are the pits. Is there an HR function?

He's obvious very, very upset at being unable to attract one of those pesky, uncooperative 'women' and rather than look to himself, he just blames them. As a woman, you are also being personally punished for it; you're the punchbag for his frustration.

I would go for dismissal and humiliation. The 'let me stop you there' line or insults are brilliant, but show you've been rattled. Something along lines of tinkly little laugh 'oh jeffery, you do talk a lot of shite* as suggested is perfect.

I would not say anything more then “you have much to learn about women” and put my headphones back on. Rinse, repeat.

Your manager is actually showing his own sexism when he says “I have not noticed!”. No shit, he is not the target of it and two, he should notice that you have told him.

If you must indulge in a spot of pig wrestling, limit it to "Hmm I reckon I'm more qualified than you to know how women think. What with having a vagina and all. Anyway, we ought to get back to work". I use this last line to shut down annoying conversations at work.

I'd get a notebook and every time he says something like this, very visibly write it down. Every so often say 'sorry what was that again, women don't like...?' and be clear that you're writing what he's saying. It totally puts the wind up people if they think you're writing their words down. They shut up pretty darn fast IME.

You don't have to attend every argument you are invited to, OP.

He's a classic Incel. I'd step away.

'No woman wants me so women must be bad at choosing'. 'Some women say they don't want an arse but I know they do really so the fact that I am behaving like an arse and am still alone PROVES that women won't admit to what they want'. etc etc

Incel or troll.

Do not engage the little creep.

He's trolling you for fun.

Ignore ignore ignore.

Do not engage in conversation. One word, closed answers if you have to.

"He is young (25) and single but desperate for a girlfriend"

I think with views like his, he may be waiting for some time.

Agree with PPs recommending the grey rock method. Ignore if you can. If you can't, respond flatly, unemotionally and repetitively. End the conversation as quickly as possible.

The original article about grey rocking is here:

180rule.com/the-gray-rock-method-of-dealing-with-psychopaths/

Grey rock and boundaries.

It's the work place so limit all conversations that are inflammatory, personal, political. Lots of good strategies from the wise women on here.

If I responded at all it would be:
"Really? Would you excuse me.." then go back to work, walk off, etc

I wouldn't engage with him about anything other than work related issues.
He has nothing of merit to say, but listening to him will probably end badly, one way or another.

"Strange that someone who supposedly knows more about what women want than me, a woman, doesn't have an actual girlfriend. Maybe you don't know quite as much as you think?"

I met a few like that. I'd just ignore, never engage with them, play dump with them and play the "girl" card all the time, get promoted above them and keep ignoring with a smug smile.
Works a charm.

Could it be a very poor attempt at flirting?

Don't rise to it...he's trying to wind you up. He wants to debate with you but remember you can't argue with stupid.
Just nod sympathetically at him when he talks shit.

I'd just give him loads of stick back. I'd say something like "oh, you are an expert on women are you?" and laugh or say something like "well, if you know them so well why are you single?"

You could say 'if I want your opinion about women I will ask you for it'
And then just go back to your day